First synthesis of macrocycles by quadruple SRN1 reactions

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1603-1604

  Beugelmans, René ^a   Chbani, Mohamed ^a   Soufiaoui, Mohamed ^b  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^b FACULTÉ DES SCIENCES   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029944383     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00077-9     Document Type: Article

References (7)

1. RN1 Mechanism. ACS Monograph 178, Washington DC, 1982.
2. •- (eq 4′) occur, which are both termination steps leading to ArH or ArSH respectively. (Formula Presented)
3. Pierini, A.B., Baumgartner, M.T. and Rossi, R.A. J. Org. Chem., 1987, 52, 1089-1092.
4. Beugelmans, R. and Ginsburg, H. Tetrahedron Lett., 1987, 28, 413-414.
5. 1H NMR signals are observed for 2 (3,7, t, 8H, J = 6 Hz); 4 (2,85, m, 8H); 6 (3,41, t, 8H, J = 6 Hz); 8 (3,06, m, 8H). Bis-sulfides 3 and 5 are identical to samples of the previous study (Ref. 4). In all experiments, secondary products (oligomers ?) were observed, but are not yet characterized.
6. •-. The fact that bis-sulfides are the major products might be due to intramolecular, and therefore very efficient electron transfer along pathway B.
7. RN1 reaction of organic halides", Chap. 24 in Supplement D2 : The Chemistry of Halides, pseudo Halides and Azides (Ed. S. Patai and Z. Rappoport), J. Wiley and Sons, Chichester, 1995, p. 1395.